3-Alpha-Hydroxy-7-oxo-5beta-cholanic acid - Moligand™,≥98% , CAS No.4651-67-6

CAS: 4651-67-6 Cat. No.: A184646 Molecular Weight: 390.6 EC Number: 225-083-2

GRADE & PURITY Moligand™, ≥98%

Synonyms

(R)-4-((3R,5S,8R,9S,10S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid | Y1357H1A28 | 3.ALPHA.-HYDROXY-7-OXO-5.BETA.-CHOLIC ACID | 3I+/--Hydroxy-7-oxo-5I(2)-cholanic acid | Cholan-24-oic acid, 3-h

Storage

Room temperature

Shipped In

Normal

Overview

7-Ketolithocholic acid (3α-Hydroxy-7-oxo-5β-cholanic acid), a bile acid, can be absorbed and suppresses endogenous bile acid production and biliary cholesterol secretion.

Specifications

Synonyms

(R)-4-((3R, 5S, 8R, 9S, 10S, 13R, 14S, 17R)-3-Hydroxy-10, 13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid | Y1357H1A28 | 3.ALPHA.-HYDROXY-7-OXO-5.BETA.-CHOLIC ACID | 3I+/--Hydroxy-7-oxo-5I(2)-cholanic acid | Cholan-24-oic acid, 3-h

Specifications & Purity

Moligand™, ≥98%

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488189825
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488189825
• Canonical Smiles: CC(CCC(=O)O)C1CCC2C1(CCC3C2C(=O)CC4C3(CCC(C4)O)C)C
• IUPAC Name: (4R)-4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• InChIKey: DXOCDBGWDZAYRQ-AURDAFMXSA-N
• INCHI: 1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-19,22,25H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,22+,23+,24-/m1/s1
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C(=O)C[C@H]4[C@@]3(CC[C@H](C4)O)C)C
• Molecular Weight: 390.6

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Bile acids, alcohols and derivatives
        • Level5 Hydroxy bile acids, alcohols and derivatives
          • Level6 Monohydroxy bile acids, alcohols and derivatives

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Bile acids, alcohols and derivatives
• Intermediate Tree Nodes: Hydroxy bile acids, alcohols and derivatives
• Direct Parent: Monohydroxy bile acids, alcohols and derivatives
• Alternative Parents: 7-oxosteroids 3-alpha-hydroxysteroids Secondary alcohols Ketones Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Monohydroxy bile acid, alcohol, or derivatives - 3-hydroxysteroid - Hydroxysteroid - 7-oxosteroid - 3-alpha-hydroxysteroid - Oxosteroid - Cyclic alcohol - Secondary alcohol - Ketone - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxide - Alcohol - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
• External Descriptors: C24 bile acids, alcohols, and derivatives

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 390.600 g/mol
• XLogP3: 4.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 390.277 Da
• Monoisotopic Mass: 390.277 Da
• Topological Polar Surface Area: 74.600 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 645.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Meng Yang, Xiaoqi Zheng, Jiajun Fan, Wei Cheng, Tong-Meng Yan, Yushan Lai, Nianping Zhang, Yi Lu, Jiali Qi, Zhengyi Huo, Zihe Xu, Jia Huang, Yuting Jiao, Biaodi Liu, Rui Pang, Xiang Zhong, Shi Huang, Guan-Zheng Luo, Gina Lee, Christian Jobin, A. Murat Eren, Eugene B Chang, Hong Wei, Tao Pan, Xiaoyun Wang.  (2024)  Antibiotic-Induced Gut Microbiota Dysbiosis Modulates Host Transcriptome and m6A Epitranscriptome via Bile Acid Metabolism.  Advanced Science,      [PMID:38713722] [10.1002/advs.202307981]

2. Qian Fang, Xiaoying Hou, Limei Fan, Yufei Deng, Xiaoxuan Li, Hongyun Zhang, Haiping Wang, Zhengqi Fu, Binlian Sun, Xiji Shu, Hongzhi Du, Yuchen Liu.  (2025)  Gut microbiota derived DCA enhances FOLFOX efficacy via Ugt1a6b mediated enterohepatic circulation in colon cancer.  PHARMACOLOGICAL RESEARCH,      [PMID:39894186] [10.1016/j.phrs.2025.107636]